Exiled/ crazy(?) Tos Starfleet Officer

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A couple friends and I are in a debate over who Benedict Cumberbatch's character might be if he was someone from or conected with TOS and all of us know who we're talking about but cannot remember who or what episode. In the episode Kirk beamed down to a prison or asylum on a planet, and ran into a man that had been a bit of a ledgend in Starfleet but was now an inmate there because of his actions that had cost him his career and put him there. I want to say that there was something going on with the running of the place that had brought the Enterprise there to investigate. No it isn't Dagger of the Mind that was my first thought but whoever it is that I'm thinking of was a major character in the episode and still acted like he was in Starfleet. Can Anyone either tell me the name of the episode and or the character? thanks for any help Chaos32 (talk) 02:36, December 9, 2012 (UTC)